Reaction equation
O=[C:2]([CH2:7][CH3:8])[C:3]([O:5][CH3:6])=[O:4].C1(C)C=CC=CC=1.[NH:16]1[CH2:20][CH2:19][CH2:18][C:17]1=[O:21].O=P(Cl)(Cl)Cl>O>[O:21]=[C:17]1[CH2:18][CH2:19][CH2:20][N:16]1/[C:2](=[CH:7]\[CH3:8])/[C:3]([O:5][CH3:6])=[O:4]Participants
Procedure
A 100 ml flask fitted with a magnetic stirring bar and a Dean-Stark trap was charged with methyl 2-oxobutanoate (7.5 g, 73 mmol), toluene (50 ml, 7 vol) and 2-pyrrolidinone (8.4 ml, 111 mmol, 1.5 equiv) followed by dropwise addition of POCl3 (1.6 ml, 20 mmol, 0.27 equiv). The reaction mixture was stirred under reflux with azeotropic removal of water via the Dean-Stask trap for 8 hours. After cooling down the solution was washed with 10% aq KHSO4 (2×3 vol). The aqueous phase was saturated with NaCl and back extracted with toluene (1×6 vol). The combined organic phase was dried over MgSO4, filtered and concentrated in vacuo to afford crude material (7.5 g) as an orange mobile oil. The crude oil was distilled (92-94° C., 0.1 mm Hg) and gave pure product (4.7 g, 60%) as a colourless oil.
Workup
- customA 100 ml flask fitted with a magnetic stirring bar
- temperatureAfter cooling down the solution
- washwas washed with 10% aq KHSO4 (2×3 vol)
- extractionback extracted with toluene (1×6 vol)
- dry with materialThe combined organic phase was dried over MgSO4
- filtrationfiltered
- concentrationconcentrated in vacuo
- customto afford crude material (7.5 g) as an orange mobile oil
- distillationThe crude oil was distilled (92-94° C., 0.1 mm Hg)
Sources & evidence
- ORD record
- ord-fbe9a53636c443c3a630486f6d995943
- Source dataset
- uspto-grants-2004_03
- Patent number
- US06713635B2
Linked notes
Loading…